Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined. Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule. If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive. If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 1

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Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 2

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 3

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 4

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 5

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 6

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 7

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 8

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 9

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 10

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 11

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 12

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Answer 13

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Answer 15

Ch. 5.1 - Prob. 5.3E Ch. 5.1 - Prob. 5.4E Ch. 5.1 - Prob. 5.5E Ch. 5.2 - Prob. 5.6E Ch. 5.2 - Prob. 5.8TIY Ch. 5.3 - Prob. 5.9E Ch. 5.3 - Prob. 5.11TIY Ch. 5.3 - Prob. 5.12E Ch. 5.4 - Prob. 5.13E Ch. 5.4 - Prob. 5.14E

Solution Summary: The author explains that halogenation products are governed by achirality or already present stereocenter in the molecule.

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